Benzoylecgonine hydrochloride

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571082

CAS#: 39426-98-7

Description: Benzoylecgonine hydrochloride is the HCl salt form of the major metabolite of cocaine (benzoyl methyl ecgonine). It is used to test presence of cocaine in drug tests, and has been investigated as a topical pain medication.


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Benzoylecgonine hydrochloride is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571082
Name: Benzoylecgonine hydrochloride
CAS#: 39426-98-7
Chemical Formula: C16H20ClNO4
Exact Mass: 325.1081
Molecular Weight: 325.79
Elemental Analysis: C, 58.99; H, 6.19; Cl, 10.88; N, 4.30; O, 19.64


Synonym: Benzoylecgonine hydrochloride

IUPAC/Chemical Name: (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid hydrochloride

InChi Key: CMSMPZLAQCHUGM-BHARVXRSSA-N

InChi Code: InChI=1S/C16H19NO4.ClH/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10;/h2-6,11-14H,7-9H2,1H3,(H,18,19);1H/t11-,12+,13-,14+;/m0./s1

SMILES Code: [H][C@]12C[C@@H]([C@@H]([C@](N1C)(CC2)[H])C(O)=O)OC(C3=CC=CC=C3)=O.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Zenilman JM, Reichart CA, Neumann TM, Hook EW 3rd. Cocaine hydrochloride and benzoylecgonine have no in vitro inhibitory effect against Neisseria gonorrhoeae. Antimicrob Agents Chemother. 1991 Jun;35(6):1228-9. PubMed PMID: 1929267; PubMed Central PMCID: PMC284316.

2: Barbieri EJ, Ferko AP, DiGregorio GJ, Ruch EK. The presence of cocaine and benzoylecgonine in rat cerebrospinal fluid after the intravenous administration of cocaine. Life Sci. 1992;51(22):1739-46. PubMed PMID: 1435082.

3: Hamilton HE, Wallace JE, Shimek EL Jr, Land P, Harris SC, Christenson JG. Cocaine and benzoylecgonine excretion in humans. J Forensic Sci. 1977 Oct;22(4):697-707. PubMed PMID: 370332.

4: Sun QR, Xiang P, Yan H, Shen M. Determination of cocaine and benzoylecgonine in guinea pig's hair after a single dose administration by LC-MS/MS. Yao Xue Xue Bao. 2008 Dec;43(12):1217-23. PubMed PMID: 19244753.

5: Mets B, Diaz J, Soo E, Jamdar S. Cocaine, norcocaine, ecgonine methylester and benzoylecgonine pharmacokinetics in the rat. Life Sci. 1999;65(12):1317-28. PubMed PMID: 10503947.

6: Gowda DC, Ambekar SY, Gupta P, Lecchi P, Pannell LK, Davidson EA. Benzoylecgonine hydrazides: synthesis, coupling to horseradish peroxidase, and characterization of the conjugates. Bioconjug Chem. 1996 Mar-Apr;7(2):265-70. PubMed PMID: 8983349.

7: Mets B, Soo E, Diaz J, Pantuck C, Singh G, Blair IA. Chronic continuous cocaine infusion in rats: effect on urine cocaine, ecgonine methylester and benzoylecgonine concentrations and bolus-dose cocaine pharmacokinetics. J Pharm Pharmacol. 2000 Apr;52(4):389-95. PubMed PMID: 10813548.

8: Ferko AP, Barbieri EJ, DiGregorio GJ, Ruch EK. The accumulation and disappearance of cocaine and benzoylecgonine in rat hair following prolonged administration of cocaine. Life Sci. 1992;51(23):1823-32. PubMed PMID: 1435091.

9: van Harren F, Garcea M, Anderson KG, Tebbett IR. Cocaine and benzoylecgonine in serum microsamples of intact and gonadectomized male and female Wistar rats. Pharmacol Biochem Behav. 1997 Oct;58(2):421-4. PubMed PMID: 9300601.

10: Penido CA, Pacheco MT, Zângaro RA, Silveira L Jr. Identification of different forms of cocaine and substances used in adulteration using near-infrared Raman spectroscopy and infrared absorption spectroscopy. J Forensic Sci. 2015 Jan;60(1):171-8. doi: 10.1111/1556-4029.12666. Epub 2014 Nov 27. PubMed PMID: 25428273.

11: Boix C, Ibáñez M, Fabregat-Safont D, Morales E, Pastor L, Sancho JV, Sánchez-Ramírez JE, Hernández F. Behaviour of emerging contaminants in sewage sludge after anaerobic digestion. Chemosphere. 2016 Nov;163:296-304. doi: 10.1016/j.chemosphere.2016.07.098. Epub 2016 Aug 17. PubMed PMID: 27543679.

12: Spear LP, Frambes NA, Kirstein CL. Fetal and maternal brain and plasma levels of cocaine and benzoylecgonine following chronic subcutaneous administration of cocaine during gestation in rats. Psychopharmacology (Berl). 1989;97(4):427-31. PubMed PMID: 2498938.

13: Baselt RC, Chang JY, Yoshikawa DM. On the dermal absorption of cocaine. J Anal Toxicol. 1990 Nov-Dec;14(6):383-4. PubMed PMID: 2087100.

14: Le SD, Taylor RW, Vidal D, Lovas JJ, Ting E. Occupational exposure to cocaine involving crime lab personnel. J Forensic Sci. 1992 Jul;37(4):959-68. PubMed PMID: 1506838.

15: Cone EJ, Menchen SL, Paul BD, Mell LD, Mitchell J. Validity testing of commercial urine cocaine metabolite assays: I. Assay detection times, individual excretion patterns, and kinetics after cocaine administration to humans. J Forensic Sci. 1989 Jan;34(1):15-31. PubMed PMID: 2918277.

16: Cone EJ, Yousefnejad D, Hillsgrove MJ, Holicky B, Darwin WD. Passive inhalation of cocaine. J Anal Toxicol. 1995 Oct;19(6):399-411. PubMed PMID: 8926734.

17: Wang WL, Cone EJ. Testing human hair for drugs of abuse. IV. Environmental cocaine contamination and washing effects. Forensic Sci Int. 1995 Jan 5;70(1-3):39-51. PubMed PMID: 7860035.

18: Kavanagh KT, Maijub AG, Brown JR. Passive exposure to cocaine in medical personnel and its effect on urine drug screening tests. Otolaryngol Head Neck Surg. 1992 Sep;107(3):363-6. PubMed PMID: 1408218.

19: Abel EL. Paternal behavioral mutagenesis. Neurotoxicology. 1989 Fall;10(3):335-45. PubMed PMID: 2626212.

20: Walsh SL, Middleton LS, Wong CJ, Nuzzo PA, Campbell CL, Rush CR, Lofwall MR. Atomoxetine does not alter cocaine use in cocaine dependent individuals: double blind randomized trial. Drug Alcohol Depend. 2013 Jun 1;130(1-3):150-7. doi: 10.1016/j.drugalcdep.2012.10.024. Epub 2012 Nov 28. PubMed PMID: 23200303; PubMed Central PMCID: PMC4852978.